Cheap Flights To Caribbean

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Caribbean Flights as Low as $126

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Wed, Jan 7 - Tue, Jan 13
ORD
O'Hare Intl.
SJU
Luis Munoz Marin Intl.
$126 Roundtrip, found 6 days ago
$126
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Wed, Jan 7 from O'Hare Intl. to Luis Munoz Marin Intl., returning Tue, Jan 13, priced at $126 found 6 days ago
JetBlue Airways
Tue, Mar 24 - Wed, Mar 25
ORD
O'Hare Intl.
SJU
Luis Munoz Marin Intl.
$153 Roundtrip, found 21 hours ago
$153
Roundtrip
found 21 hours ago
Select JetBlue Airways flight, departing Tue, Mar 24 from O'Hare Intl. to Luis Munoz Marin Intl., returning Wed, Mar 25, priced at $153 found 21 hours ago
Spirit Airlines
Tue, Jan 20 - Tue, Jan 27
ORD
O'Hare Intl.
SJU
Luis Munoz Marin Intl.
$198 Roundtrip, found 6 days ago
$198
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Tue, Jan 20 from O'Hare Intl. to Luis Munoz Marin Intl., returning Tue, Jan 27, priced at $198 found 6 days ago
United
Wed, Mar 4 - Wed, Mar 4
ORD
O'Hare Intl.
SJU
Luis Munoz Marin Intl.
$231 Roundtrip, found 19 hours ago
$231
Roundtrip
found 19 hours ago
Select United flight, departing Wed, Mar 4 from O'Hare Intl. to Luis Munoz Marin Intl., returning Wed, Mar 4, priced at $231 found 19 hours ago
American Airlines
Sat, Jan 24 - Sat, Jan 24
ORD
O'Hare Intl.
SJU
Luis Munoz Marin Intl.
$280 Roundtrip, found 6 days ago
$280
Roundtrip
found 6 days ago
Select American Airlines flight, departing Sat, Jan 24 from O'Hare Intl. to Luis Munoz Marin Intl., returning Sat, Jan 24, priced at $280 found 6 days ago
Spirit Airlines
Wed, Feb 18 - Wed, Feb 25
ORD
O'Hare Intl.
PUJ
Punta Cana Intl.
$289 Roundtrip, found 3 days ago
$289
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Wed, Feb 18 from O'Hare Intl. to Punta Cana Intl., returning Wed, Feb 25, priced at $289 found 3 days ago
Delta
Tue, Mar 10 - Wed, Mar 18
ORD
O'Hare Intl.
MBJ
Sir Donald Sangster Intl.
$391 Roundtrip, found 4 days ago
$391
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Mar 10 from O'Hare Intl. to Sir Donald Sangster Intl., returning Wed, Mar 18, priced at $391 found 4 days ago
Air Canada
Tue, Mar 3 - Thu, Mar 12
ORD
O'Hare Intl.
AUA
Queen Beatrix Intl.
$450 Roundtrip, found 4 days ago
$450
Roundtrip
found 4 days ago
Select Air Canada flight, departing Tue, Mar 3 from O'Hare Intl. to Queen Beatrix Intl., returning Thu, Mar 12, priced at $450 found 4 days ago

Caribbean Flights

For seniors in search of the best deals on airfares, AARP Travel Center Powered by Expedia features low-cost flights in Caribbean. Right here you may enter your expected travel dates to browse through the selection of cheap flights for seniors in Caribbean. The search engine presents a variety of low-cost plane tickets, airline carriers, and travel times to ensure the Caribbean AARP Travel Center flights suit your travel needs and preferences. And on top of affordable airline tickets, AARP members also enjoy no additional booking fees when you book your Caribbean senior flights on AARP Travel Center Powered by Expedia. These senior flights to or from Caribbean allow you to jet set without breaking the bank.